64024-63-1

Basic information

• Product Name: 4-((TRIMETHYLSILYL)ETHYNYL)MORPHOLINE
• Synonyms: 4-((TRIMETHYLSILYL)ETHYNYL)MORPHOLINE;Morpholine,4-[2-(trimethylsilyl)ethynyl]-;4-[(Trimethylsilyl)ethynyl]morpholine 97%
• CAS NO: 64024-63-1
• Molecular Formula: C₉H₁₇NOSi
• Molecular Weight: 183.32288
• Mol File: 64024-63-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 88-90 °C9 mm Hg(lit.)
• Flash Point: 174 °F
• Appearance: /
• Density: 0.931 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.078mmHg at 25°C
• Refractive Index: 1.479
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 4-((TRIMETHYLSILYL)ETHYNYL)MORPHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-((TRIMETHYLSILYL)ETHYNYL)MORPHOLINE(64024-63-1)
• EPA Substance Registry System: 4-((TRIMETHYLSILYL)ETHYNYL)MORPHOLINE(64024-63-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 64024-63-1(Hazardous Substances Data)

Usage

Uses

4-?((Trimethylsilyl)?ethynyl)?morpholine acts as a reagent in the modification of the side chain of micromolide, an anti-tuberculosis natural product, synthesis of antifugal antibiotics (+)-desoxyfugomycin and (+)-fugomycin via sonogashira alkynylation.

InChI:InChI=1/C9H17NOSi/c1-12(2,3)9-6-10-4-7-11-8-5-10/h4-5,7-8H2,1-3H3

Upstream product

• 13306-60-0 N-(trichloroacetyl)morpholine 
• 75-77-4 chloro-trimethyl-silane 
• 310905-04-5 4-((E)-1,2-Dichloro-vinyl)-morpholine 
• 60506-50-5 1,1,2-Trichloro-2-morpholinoethen 
• 110-91-8 morpholine 
• 7652-06-4 chloroethynyl-trimethyl-silane 

Downstream Products

• 415902-43-1 4-((S)-5-Phenoxymethyl-3-trimethylsilanyl-4,5-dihydro-furan-2-yl)-morpholine 
• 1243713-64-5 4-benzyl-5-(4-morpholino-1,3-dithiol-2-ylidene)-6-thioxo-5,6-dihydro[1,2]dithiolo[3,4-b][1,4]thiazin-3(4H)-one 
• 1129541-45-2 4-(1-(4-nitrophenyl)-4-(trimethylsilyl)-1H-1,2,3-triazol-5-yl)morpholine 
• 76311-90-5 5-methyl-3-bromo-2(5H)-furanone 

Relevant articles and documents

A straightforward synthesis of silylated and stannylated ynamines and ynehydrazines

Metallated ynamines 5a-f and ynehydrazines 5g,h were prepared in a very short reaction sequence by consecutive treatment of trichloroethylene (1) with the lithium salt of secondary amines or of trimethylhydrazine, 2 equivalents of butyllithium and chlorotriorganosilanes or -stannanes.

Low-energy pathway for Pauson-Khand reactions: Synthesis and reactivity of dicobalt hexacarbonyl complexes of chiral ynamines

A family of dicobalt hexacarbonyl complexes of 1-(dialkylamino)-2-(trimethysilyl)acetylenes (3a-f) derived both from achiral and chiral amines [a, morpholine; b, (S)-2-methoxymethylpyrrolidine; c, (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine; d, (±)-trans-2,5-bis(benzyloxymethyl)pyrrolidine; e, (2R,5R)-2,5-dimethylpyrrolidine; f, (S)-(α-methylbenzyl)benzylamine] has been prepared by a one-stage process from dichloroacetylene. The methanolysis at room temperature of these complexes (MeOH/K2CO3) induces the selective cleavage of the carbon-silicon bond, leading to the thermally unstable terminal ynamine complexes 12a-f. The Pauson-Khand reaction of 12a-f with strained olefins (norbornadiene and norbornene) takes place at unprecedentedly low temperatures (-35 °C) in the absence of chemical promoters. Diastereoselectivities of up to 94:6 are recorded in these reactions with the ynamine complexes derived from C2 symmetrical chiral auxiliaries (12c,d). The high reactivity depicted by terminal ynamines in the Pauson-Khand reaction has been analyzed by theoretical semiempirical procedures [PM3(tm)] and with density functional theory (VWN/B88), and appears to reflect an easy CO loss from the ynamine-dicobalt hexacarbonyl complexes.